Method of manufacturing chloro-thymol



Patented July 1,1930

unrrsu stares FRIEDRICH RASGI-IIG, or unwresnrarn -O1\T-THE-RHINE,GERMANY, nssieivon' ro DR. F. RASCHIG, 01'" LUDVIIGSHALEEN-OELTHE-RHINE,GEBMANY, A, OF.

.BAVARIA METHOD OF MANUFACTURING CHLORO-THYMOL No Drawing. Applicationfiled April 2, 1927, Serial No. 180,615, and in Germany April 29, 1926.

My invention relates to the manufacture of chloro-thymol of the formulal-methyl- 3-hydroxy-4-isopropyl-6-chloro-benzol, and more particularlyto the production of chloro-thymol from chloro-metacresol. 7

It has been proposed heretofore to manufacture thymol by sulphonatingmetacresol in order to produce cresol-sulphonic acid,

treating the latter with iso-pr'opylic alcohol in presence ofconcentrated sulphuric acid and separating out the sulpho-group in theusual manner. In following this course, however, a byproduct is formedwhich is of isomeric character, as regards. 1 thymol, and of a somewhathigher boiling point than the latter while its crystallizing point liesat or near 11 1 to 115 C.

In another known process for theformation of thymol phosphoric acid isemployed as a condensing agent and also in this case an isomericcompound having a melting point of 11 .1 C. results which sometimesforms a larger proportion of the output so as to constitute the mainproduct.

Now, I have found that by condensing chloro-metacresol of the formulal-methyl- 3-hydroxy-6-chloro-benzol in a similar manner by means ofisopropylic alcohol, almost exclusively chloro-thymol of the formula 1-Inethyl-8-hydroxyl-isopropyl-G-chloro-benzol is'formed and no chlorinederivatives of any other iso-propylic metacresol occur or can be foundto exist in the reaction product. This matter of fact is certainlysurprising viewing the state of the art as above disclosed.

Chloro-thymol of the character herein described or as formed accordingto my in vention is known in itself. It has been first manufactured byBocchi, see Gazetta chemica italiana, 1926, II. 163 u. C. 1907 I 38.Characteristic features thereof are the melting point of 62 to 64 C. andan im- I mense bactericidal or antiseptic potency so 'that'even'asaturatedaqueous solution thereof, though only .03 per cent of thecompound are contained therein, will be of a strength sufficient formost disinfecting or germicidal purposes.

I shall now proceed toexplain my im-' proved method more in detail toenable those'skilled in the art to understand howv my inventionmay beused-in certain ofits preferred forms, I wish it to be understood,

' however, that such preferred forms are detion upon the scope of theappended claims as the right is reservedto modifications and variationsto the full extent indicated by the general meaning of the terms inwhich the claims are expressed.

I prepare first, at a temperatureof to (1, a mixture consisting of 240parts by weight of iso propylicalcohol and 600 parts by weight ofsulphuric acid monohydrate,

and I pour the mixture or cause the same to iiow slowly,jthat is withina full hour, into 1000 parts by weight of l-methyl-S-hydroxy-6-chloro-benzol, keeping the liquid under treatment at a temperature ofC. and

.stirring'the same incessantly by means of water and allow the same tostand over night. at a temperature of C;

liquid comprises two dis- The resulting tinct layers. The one layer ofoily nature containing .chloro-metacresol and the desired chloro-thymolis separated from the other or aqueous layer and the oily substance issubsequently washed with water to remove allfree acid whereupon the sameis subjected to a fractional distillation which is to be'carried out inthe usual manner so as not.

to deserve d'escription in detail.

Theoutput amounts to 350 parts by 5 weight of pure chloro thymol and 500parts by weight of pure chloro-metacresol' which are to be returned forrepeated use. p

f Example 2 I mix 1000 parts by weight of chlorometacresol with 300parts by weight of a temperature of 80 (J. I then cause 500 partsbytweight of iso-propylic Chloride to slowly flow into the mixturewithin one hour keeping the temperature at 80 to 90 C.

The hydrochloric acid evolved by the r'eaction escapes and togethertherewith about :200 parts by weight of iso-propylic chloride willescape which, however, are recovered I andinay be againused in thenext'mixin'g 1 I operation- The resultingf reactionproduct i is Washedout with water for the purpose of removing, all free -chloride of*Zincand hydrochloricacid therefrom and the remaining productis-subje'cted to fractional distillation. i

of :pure chloro-thymol and 500 parts by 'weightl of purechloro-metacresolwhichare V V returned for use- 11i the next II11XlIlg"operation H WhatIclainiiSE o '1; (1111 Qniethodof producing ehloro-lthyn ol of the formula 1-methyl-3'hydrozcy ie iso'propyl-(i 'chlorobenz'ol;Which comprises treating, chloroinetacresol ofthe forniula (CI-IQ 'CHXin which X i may be halogen or h yclroxy in the presence 'of an acidiccondensing agent, and separating the chloro-thyinol thus forined bycondensation residual chlorof neta:

cresolwl,

"2.,The method of producing chlorothyr nol of the formulal-methyl-3-hydroxy1 -akisopropyl-6-chloroibenzol, which comprises iitreating. ochloro-rnetacresol with iso propyl Y chlorideingthepresenceofa haloid salt of the heavyn etals, and separating thechlorothymol thus formed by condensation, from theresidualchloro-metacresoli V 3. The method of producing chlorothyrnolofthe formula 1-,methy1-3-hydroxy- 4-isopropyl 6-chloro benzol,

formedby condensation, from the residual chlorqimetacresol.

Si natur 1 a FRIEDRlCI I RASCl IIG.

The output ainounts to 400 parts by weight with a compound whichcomprises treating chloro n etacresol with Visopropyl chloride inthepresence of chloride of zinc, and separating the chloro-thyniol thus

